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The House Always Wins…Unless You’re Penn Entertainment ($PENN)
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The House Always Wins…Unless You’re Penn Entertainment ($PENN)

A digital business misfire, activist pressure, and Boyd circling—what it means for shareholders and bondholders

Feb 22, 2025
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The House Always Wins…Unless You’re Penn Entertainment ($PENN)
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🚨 Connect with me on Twitter / Instagram / Threads / Bluesky | Estimated Read Time: 17 Minutes


You want to know what delusion looks like?

Watch a casino company blow billions chasing sports betting dreams, give Barstool back to Dave Portnoy for ONE DOLLAR, then try to tell shareholders everything’s fine.

But the music’s finally stopping at Penn. Activist investor, HG Vora, just nominated 3 directors for the board. And if you think this is just another activist making noise, you haven’t been paying attention.

The setup couldn’t be better. You’ve got a stock that’s undervalued, a core business that throws off cash, and an opportunity for change that Wall Street is basically begging for.

HG Vora isn’t here to make suggestions—they’re here to take control. Management spent the last year trying to keep them off the board, because they know what happens once the grown-ups step in.

No, the real question is what happens next. Does Boyd Gaming, who’s been circling the company like a vulture, finally swoop in now that there’s blood in the water?

Or maybe Penn finally throws in the towel on sports betting. They could wind down ESPN Bet—the contract has an out in 2026 anyway. Focus on their actual profitable casino business. Start returning capital to shareholders instead of lighting it on fire.

And for bondholders? A cleaner balance sheet, lower leverage, and a real casino company instead of a failing tech startup.

This isn’t about whether shareholders win—they will. It’s just about how much they win by and what this may mean for existing creditors.

Let’s find out.

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